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<h1><a href="https://archiveofourown.org/works/23766910">Midtown Manhattan</a> by <a class='authorlink' href='https://archiveofourown.org/users/mexican_torpedo/pseuds/mexican_torpedo'>mexican_torpedo</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Alternate Universe: Modern Day, Businessman Dean, Castiel is busy, Dean is a rich and lonely man, FBI Agent Castiel, Lawyer Sam, M/M, Sam is vibing, no monsters, way more to come - Freeform</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>In-Progress</td></tr>

<tr><td><b>Published:</b></td><td>2020-04-21</td></tr>

<tr><td><b>Updated:</b></td><td>2020-06-18</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-02 18:21:37</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>3</td></tr>

<tr><td><b>Words:</b></td><td>2,865</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/23766910</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/mexican_torpedo/pseuds/mexican_torpedo</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Dean Winchester, built a successful business and is on his way to becoming the most successful man in New York, yet with success comes loneliness. His lawyer brother Sam helps him along the way. Castiel Novak is sent undercover to investigate a major crime organization hiding in the shadows of New York. What will Castiel find? Will Dean ever find a cure to his despair?</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester, Dean Winchester &amp; Sam Winchester</td></tr>

<tr><td><b>Comments:</b></td><td>1</td></tr>

<tr><td><b>Kudos:</b></td><td>9</td></tr>

</table>

<a name="section0001"><h2>1. Glass Windows</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Hey all! This is my first attempt at a long-ish fic. I do plan on adding more chapters every week, I currently am working on more. I dunno how long this will be or what even happens, but I'm open to suggestions! Enjoy this quick first chapter and tell me what you think.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>The night skyline never ceases to capture his gaze. New York is beautiful at night; the glimmers from the taller buildings jutting out above the smaller ones and the rows and rows of skyscrapers create the perfect picture. </p>
<p> </p>
<p>Dean Winchester stands in his 16th floor penthouse living room. Its the top floor of a luxury apartment building. He stares out of his gigantic glass windows, mind clouded and hazy. From the horizon he can see a storm rolling in. His favorite weather.</p>
<p> </p>
<p>Eight years ago, Dean never would have thought he’d be where he is right now. Almost yesterday he remembers going to drop off his brother Sam to college. Now, Sam is grown, bigger than him, and is one of the most up to date successful lawyers in New York. </p>
<p> </p>
<p>Dean’s idea of taking over their late father’s business didn’t seem like it would get this big. At twenty he renovated his father’s automobile designs and contacted engineers and it went from there. Now at 30, he’s a high end mechanical engineer, entrepreneur, and CEO of his own multi-million dollar business company. Then his baby brother graduated law school and decided to help Dean out with legalities; now they’re a dynamic duo. </p>
<p> </p>
<p>But Dean can’t shake the feeling of uneasiness. He takes his suit jacket off and undoes his tie, laying them on the railing in front of his window. Today was the meeting for their biggest deal yet. An offer of 25 million in funding they couldn't refuse. Dean should be ecstatic, yet he’s not. It’s just more years of meetings and rich people that only talk to him for his business. </p>
<p> </p>
<p>Rubbing his eyes, Dean takes in the melancholy view one last time before he heads upstairs to his bedroom. He bypasses the enormous kitchen he never uses and the other living room few other eyes have seen. </p>
<p> </p>
<p>‘I gotta do something different,’ he thinks to himself, ‘this isn’t me.’</p>
<p> </p>
<p>The water is warm as it slides down his face, rolling down on his body. Dean takes his time, it's not like he has anywhere to be. He ponders on what he wants. There’s not much, he just doesn’t like the sameness of his life. </p>
<p> </p>
<p>He gets out and follows his routine for bed. Settling down on the king-size, he drifts off wondering what could help him. </p>
<p> </p>
<p>-</p>
<p> </p>
<p>It does rain the next day, not heavy but a constant drizzle and it's chilly. Before he heads out, Dean grabs a long black peacoat and descends down the elevator in the penthouse. </p>
<p> </p>
<p>As always, his driver and escort are waiting for him in the lobby, suits intact with Dean’s usual coffee order. They settle in the car and venture about 20 minutes before reaching the business in Midtown Manhattan. It doesn’t matter what condition the city is in, the constant bustle of people is everywhere. </p>
<p> </p>
<p>By the time Dean reaches his office, Sam is waiting for him inside.</p>
<p> </p>
<p>“You know, just because you're my brother doesn’t mean you get to break into my office,” Dean has a bit of annoyance in his voice, but can’t help but smile.</p>
<p> </p>
<p>“Dude, you gave me a set of keys” the annoyance is also in Sam’s voice but is more fond. “Anyway, did you close on that deal yesterday?” There’s excitement in his eyes.</p>
<p> </p>
<p>“Yes I did, though there’s no reason why I wouldn’t,” Dean explains earnestly, “It's a killer deal.”</p>
<p> </p>
<p>“Obviously,” Sam smirks, “We’re going out to celebrate tonight.”</p>
<p> </p>
<p>Dean’s stomach does a little flip.</p>
<p> </p>
<p>“No, there’s no need for-”</p>
<p> </p>
<p>“I’m not asking.” The firmness in his brother’s voice lets him know there’s no way out of this situation. </p>
<p> </p>
<p>Not content, Dean’s bitch-face let’s Sam know what he’s feeling.</p>
<p> </p>
<p>“C’mon! I see how you’re moping around all day and you never make plans and you’re lonely,” he makes sure to emphasize lonely, “You need to get out every once in a while.” Sam looks like he’s serious and sounds like it too.</p>
<p> </p>
<p>“I do not mope,” Dean said while he was, in fact, moping.</p>
<p> </p>
<p> “I’ll be back after your last meeting at 4.”</p>
<p> </p>
<p>“How do you know my last-”</p>
<p> </p>
<p>“I know lots of things Dean,” Sam’s eyes narrowed in on Dean.</p>
<p> </p>
<p>“Ew.” </p>
<p> </p>
<p>“See you later,” Sam closed the door behind him.</p>
<p> </p>
<p>Dean powered up his computer system already dreading the evening to come. Going out is never really any trouble for him, but he just does not feel up to it. Maybe Sam is right. Maybe he is lonely. </p>
<p> </p>
<p>‘Nah, that can’t be it… Can it?’ The screen lit up and soon Dean forgot about his personal life and let himself be carried away by his work. </p>
  </div></div>
<a name="section0002"><h2>2. Something Suspicious</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Castiel discovers a new clue in his investigation.</p>
          </blockquote><b>Notes for the Chapter:</b><blockquote class="userstuff"><p>Hey y’all here’s chapter 2. I know cops are a sensitive subject but I started this a while before current world events, so please go along it’s just  a fanfic and doesn’t really reflect my personal views at all it’s just for the story. If y’all have any suggestions lmk!</p></blockquote></div><div class="userstuff module">
    
    <p> </p><p>Life in New York City isn’t easy especially for a cop, let alone an undercover agent. Castiel Novak learned that pretty quickly after being handed a special assignment. </p><p> </p><p>He’d graduated top of his class in the academy, then was recommended to the higher authority. Castiel made high ranking in the Federal Bureau of Investigation and instead being a boy in blue, turned out to be a man in black. Sort of. </p><p> </p><p>He’s the best of the best. Top scores in all areas: criminal justice, forensics, public safety, you name it. And he landed in Times Square. Undercover. As a detective. </p><p> </p><p>Granted, he knew the case’s major secrets that needed to be exploited, so that gave him an advantage. The New York Police Department in Manhattan is one of the highest rated police departments that actually do their work, and his “co-workers” are decent. </p><p> </p><p>Castiel’s gotten used to the algorithm in the city. Nothing really surprises him anymore; he’s seen it all. Beautiful Macy’s parades to gruesome hit-and-runs, twelve months on an investigation will do that to an agent. </p><p> </p><p>At the department, Castiel walks in, a bit muddled from the rain, and meanders to his desk. Setting his coffee down, he sees Chuck Shurley heading towards him. </p><p> </p><p>“Hello, boss,” Castiel’s gravelly voice greets.</p><p> </p><p>“Morning Jimmy! How’s the case coming along?” Bouncing on his feet, Chuck seems anxious about something.</p><p> </p><p>A tad suspicious, Castiel hesitates, forming carefully a summation of current events. After all, they don’t know what ‘Jimmy’ is really up to, though this is the closest he’s been in rounding up leads for the Feds. </p><p> </p><p>“I discovered plans for the operation to expand last week,” Chuck’s shoulders relaxed, “I’m trying to get my hooks in, but they’re good at covering their tracks.” Castiel can’t help but look off in thought. </p><p> </p><p>“Uh, right.” The boss always makes things awkward for no reason. “Well continue the good work, I was worried we might need to bring in more eyes.”</p><p>“That won't be necessary,” Castiel’s gaze bolts right back to Chuck and narrows in on him, making Chuck slightly nervous. </p><p> </p><p>“Oh-kay. Good talk,” the anxiety never misses a bit while Chuck forces out a laugh and goes toward his office.</p><p> </p><p>“How is this man chief of police and head of a precinct…” Castiel mumbles as he gets started for the day. </p><p> </p><p>-</p><p> </p><p>“How ya doin’ Jim?” It's barely nine when Garth comes stumbling to his desk. The detective is always full of energy and beaming with a smile. </p><p> </p><p>“Working,” Castiels says bluntly, eyes not leaving the monitor. He’s just found an article explaining a new business deal for a company in Midtown. </p><p> </p><p>“Always so hard at work,” Garth’s eyes soften up at his co worker's actions. “Do you ever give yourself a break?”</p><p> </p><p>“Don’t need one,” looking up sharply, Castiel tries to be nice and give him a hint that he just wants to get his stuff done. “Thanks for asking,” and he returns to the article.</p><p> </p><p>“No problemo, comrade,” joy and happiness ever present in Garth’s voice. He does take the hint, though, and goes to his desk in the next row. </p><p> </p><p>Castiel’s mind is a blizzard, trying to figure out why this article seems so suspicious and sticks out. He’s seen the CEO of the company Winchester Auto and he’s done his basic research; it’s a clean company. What he hasn’t seen is the organization that he made the deal with. </p><p> </p><p>‘Time to do what I was sent here for’ the FBI side of Castiel makes the decision for him.</p><p> </p><p>“Garth,” he says monotonously above his monitor.</p><p> </p><p>“Yes?” comes the eager reply. </p><p> </p><p>“Cover for me.” With that, Castiel slings his jacket over his shoulders and heads to Midtown. </p><p> </p><p>-</p>
  </div></div>
<a name="section0003"><h2>3. Digging Deeper</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Dean is questioned by a mysterious detective. Who has really nice eyes.</p>
          </blockquote><b>Notes for the Chapter:</b><blockquote class="userstuff"><p>Chapter three is up. I'm not sure how I feel about this one since its longer, but feedback is accepted. Enjoy.</p></blockquote></div><div class="userstuff module">
    
    <p>
  <span>The building is bustling after news of the successful deal spread. The sound of keyboards clacking and mouses clicking is slightly more noticeable as Dean prepares his lunch in the upscale break room down the hall from his office. Food is an essential and Dean had the room specifically built for his wants and needs. He feels a presence behind him and grabs his plate of salad and greens before he turns around. </span>
</p><p> </p><p>
  <span>Dean’s a bit taken back by who he sees standing under the door frame. The man has the bluest eyes he’s ever seen and the messiest yet nicest hair, too. On top of that, he has a professional suit and strong posture. </span>
</p><p> </p><p>
  <span>“Hello Mr. Winchester,” his voice brings shivers down the CEO’s spine, “I noticed you weren’t in your office but I heard some noises down the hall so I came to try and find you.” </span>
</p><p> </p><p>
  <span>‘Weird that he knows my name,’ Dean thinks, ‘But then again I am the owner of a big company.’</span>
</p><p> </p><p>
  <span>“Um, yes I’m just on my lunch break,” Dean doesn’t really know what to say, as he’s caught off guard, “Dean Winchester, and you are?” he introduces himself after he sets his plate down and reaches his hand out while walking closer to the man. </span>
</p><p> </p><p>
  <span>“My name is Jimmy Smith,” the man accepts the greeting and looks Dead confidently in the eyes, “I’m a detective with the NYPD and I was hoping you could answer a few questions.” Jimmy’s voice is deep and demanding as he pulls his jacket back to reveal his badge. </span>
</p><p> </p><p>
  <span>“Was my secretary unable to answer your questions?” Dean doesn’t sound rude, just concerned that the NYPD shows up in his lunch room. </span>
</p><p> </p><p>
  <span>“Ah, I apologize for the sudden intrusion. She told me I was welcome to ‘attempt’ to speak with you; although I think she was being sarcastic,” Jimmy explains a bit abashed. “Its nothing serious, I just have some questions about a business deal you’ve recently made.”</span>
</p><p> </p><p>
  <span>‘Sounds pretty damn serious to me,’ Dean doesn’t want a bad rep, so he figures its best to comply. </span>
</p><p> </p><p>
  <span>“I’ll be happy to answer any questions as long as my lawyer is present,” Dean tries to come across as helpful but Jimmy’s expression of neutrality falters a bit</span>
</p><p> </p><p>
  <span>“Of course, Mr, Winchester. Whatever is comfortable for you,” the detective steps aside and Dean shrugs a bit and walks to grab his plate. </span>
</p><p> </p><p>
  <span>When he turns around, he swears the detective has a smile on his face but it disappears as Dean walks closer. </span>
</p><p>
  <span>“Follow me.” </span>
</p><p> </p><p>
  <span>Once inside Dean’s office, he gestures for the detective to sit on one of the luxurious chairs in front of his oak desk. Dean sets his plate down and then himself while he phone his brother from the floor underneath.</span>
</p><p> </p><p>
  <span>“Thank you for being patient, my lawyer will be here shortly.” Dean is a bit nervous because he has no clue what he’s being questioned for. </span>
</p><p> </p><p>
  <span>Jimmy just nods his head and looks past him through the glass windows that look onto the city while Dean enjoys his first bite of his salad, unbeknownst when Jimmy takes a few quick glances back. </span>
</p><p> </p><p>
  <span>Thankfully breaking the silence, there’s a knock on the door and footsteps coming over.</span>
</p><p> </p><p>
  <span>“Hi,” comes from a tall man in a neatly pressed suit, “I’m Sam Winchester, Dean’s lawyer,” he shakes Jimmy’s hand.</span>
</p><p> </p><p>
  <span>“Detective Jimmy Smith. I just have a few questions for Mr. Winchester.” Sam sits next to Jimmy and looks at Dean for confirmation on the situation. Dean nods his head. </span>
</p><p> </p><p>
  <span>“Well what can we do for you, Detective Smith?” Sam asks as he takes out his notepad and begins writing. </span>
</p><p> </p><p>
  <span>“I have reason to believe that the company you recently made a deal with is a suspect of the NYPD. I-” Jimmy is cut off by Sam.</span>
</p><p> </p><p>
  <span>“Can you inform me of the reason for suspicion?” Sam raises his eyebrows as Jimmy turns back to Sam.</span>
</p><p> </p><p>
  <span>“I cannot explain in full detail without permission from the chief to let you in on the case yet, but I can let you know that companies who offer multi-millions to big successors are on the radar in the precinct,” he explains carefully as Sam writes and nods his head for him to continue. Jimmy turns back to Dean.</span>
</p><p> </p><p>
  <span>“Have you had any connection to this company for over 6 months?” </span>
</p><p> </p><p>
  <span>“Just little contact through assistants here and there, but the contact wasn’t serious until about three weeks ago when they began to ask about offers and contracts.” Dean remembers these things, mainly because he has nothing else to remember in his life. </span>
</p><p> </p><p>
  <span>“Okay, now has the offers come from multiple people from the organization, or just one person?” Jimmy’s eyes never leave Dean’s. </span>
</p><p>
  <span>“Come to think of it, I have noticed my secretary tell me how different voices on calls sometimes have different offers.” Sam’s face shoots up at Dean’s with a bit of concern on them.</span>
</p><p> </p><p>
  <span>“Is this a sign of something wrong with the company, detective?” Sam presses seriously.</span>
</p><p> </p><p>
  <span>“Yes, but that’s why I need to ask questions; to find out if this is characteristic of the specific organizations under investigation,” Jimmy explains very patiently, still focusing on Dean.</span>
</p><p> </p><p>
  <span>‘Jeez this guy’s gaze is giving me goosebumps,’ Dean notes to himself.</span>
</p><p> </p><p>
  <span>“Can I ask the name of the organization who offered you the deal and why you chose this company?”</span>
</p><p> </p><p>
  <span>“The company is called Demonegy and they were persistent on making a deal. They kept making higher offers when we declined and finally they made an offer we couldn’t resist.” Dean is a bit apprehensive while answering the question but Sam doesn’t seem to have any objections. </span>
</p><p> </p><p>
  <span>“Last question: Can you tell me the name of the owner of Demonegy?” Now Jimmy turns to look at Sam, who nods his head. </span>
</p><p> </p><p>
  <span>‘This is a lot of info that hasn’t been shared to the public yet…” Dean thinks and stands up.</span>
</p><p> </p><p>
  <span>“Excuse us for a second,” Dean gives a fake smile as he’s alarmed and gestures for Sam annoyingly. </span>
</p><p> </p><p>
  <span>“Why are we giving him this info!” he whisper-screams by the door. </span>
</p><p> </p><p>
  <span>“Calm down dude!” Sam retaliates with the same energy, “I’m not trying to involve you in any crime business, so play along unless you want to be under investigation!” Rolling his eyes, Sam heads back to the desk.</span>
</p><p> </p><p>
  <span>Dean makes a bitch-face but as he goes back he realizes that Sam’s right.</span>
</p><p> </p><p>
  <span>“Our business partner is Crowley Roderick. His team is pretty anonymous, but from what we’ve researched about them, they’re an organization that mainly makes investments,” the answer is as straightforward as Dean can get. </span>
</p><p> </p><p>
  <span>Jimmy sits there staring at Dean, more than Dean is used to, which gives Dean a bit of time to take in his features. The detective’s 5 o’clock shadow brings out his jawline and his chapped lips are slightly pink. </span>
</p><p> </p><p>
  <span>‘Not bad…’ Dean trails off before Jimmy stands up abruptly. Dean blushes a little as he realizes he was also staring back.</span>
</p><p> </p><p>
  <span>“Thank you so much gentlemen,” the detective says as he shakes Sam’s hand and then Dean’s, “This is valuable information. Please call me if you have any other details you would like to share,” then hands him a business card. </span>
</p><p> </p><p>
  <span>“Of course,” Dean reaches down for his own card before handing it to the detective. “We’d be happy to cooperate with any further questioning. We’re a clean company and would like to keep it that way.” Dean smiles at Jimmy and is relieved to see a small smile in return. Sam raises his eyebrows a bit knowingly. </span>
</p><p> </p><p>
  <span>“I’ll show myself out. Have a pleasant lunch, Mr. Winchester.” He nods to Sam and walks out of the office. </span>
</p><p> </p><p>
  <span>Dean is still looking at the door when Sam walks in front of his line of vision. </span>
</p><p> </p><p>
  <span>“Hellooo. Earth to Dean?” Sam laughs when his brother snaps out of it. “You okay, dude?” </span>
</p><p> </p><p>
  <span>“What are you talking about?” he says with a slight blush on his cheeks. </span>
</p><p> </p><p>
  <span>“Uhh don’t bullshit me now. I totally saw the way you gazed into his eyes!” Sam’s eyebrows were impossibly high on his face. Dean just rolled his eyes.</span>
</p><p> </p><p>
  <span>“I’m not in the mood for this right now, man. In case you didn’t notice, my company is being questioned for dirt deals!” At this point, Dean’s really agitated and is showing it. </span>
</p><p> </p><p>
  <span>“Relax,” Sam scoffed. “We made it clear that we’re cooperating. It’s okay to admit he’s hot!” Sam shrugged his shoulders as Dean rolled his eyes again. </span>
</p><p> </p><p>
  <span>“Get out of here and dig into the company.” Sam surrenders and grabs his things. “And don’t come back till you find something!” Dean shouts as Sam flips him off when he reaches the door.</span>
</p><p> </p><p>
  <span>“I don’t like the cute mysterious detective…” Dean mutters to himself as he finally gets back to his salad. </span>
</p><p> </p><p> </p><p> </p>
  </div></div>
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